Phorone A and isophorbasone A, sesterterpenoids isolated from the marine sponge Phorbas sp.

Weihong Wang; Yehee Lee; Tae Gu Lee; Bora Mun; Awadut G. Giri; Jihye Lee; Hiyoung Kim; Dongyup Hahn; Inho Yang; Jungwook Chin; Hyukjae Choi; Sang Jip Nam; Heonjoong Kang

doi:10.1021/ol3019874

Phorone A and isophorbasone A, sesterterpenoids isolated from the marine sponge Phorbas sp.

Weihong Wang, Yehee Lee, Tae Gu Lee, Bora Mun, Awadut G. Giri, Jihye Lee, Hiyoung Kim, Dongyup Hahn, Inho Yang, Jungwook Chin, Hyukjae Choi, Sang Jip Nam, Heonjoong Kang

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

31 Scopus citations

Abstract

A chemical investigation of a Korean marine sponge, Phorbas sp., yielded unprecedented sesterterpenoids phorone A (1) and isophorbasone A (2) along with ansellone B (3) and phorbasone A acetate (4). Their complete structures were elucidated by the combination of spectroscopic data and chemical manipulation. Phorone A (1) and isophorbasone A (2) have the new "phorane"(5) and "isophorbasane"(6) sesterterpenoid carbon skeletons, respectively. Ansellone B (3) and phorbasone A acetate (4) exhibited potent inhibitory activity on nitric oxide production in RAW 264.7 LPS-activated mouse macrophage cells with IC₅₀ values of 4.5 and 2.8 μM, respectively.

Original language	English
Pages (from-to)	4486-4489
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	17
DOIs	https://doi.org/10.1021/ol3019874
State	Published - 7 Sep 2012

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title = "Phorone A and isophorbasone A, sesterterpenoids isolated from the marine sponge Phorbas sp.",

abstract = "A chemical investigation of a Korean marine sponge, Phorbas sp., yielded unprecedented sesterterpenoids phorone A (1) and isophorbasone A (2) along with ansellone B (3) and phorbasone A acetate (4). Their complete structures were elucidated by the combination of spectroscopic data and chemical manipulation. Phorone A (1) and isophorbasone A (2) have the new {"}phorane{"}(5) and {"}isophorbasane{"}(6) sesterterpenoid carbon skeletons, respectively. Ansellone B (3) and phorbasone A acetate (4) exhibited potent inhibitory activity on nitric oxide production in RAW 264.7 LPS-activated mouse macrophage cells with IC50 values of 4.5 and 2.8 μM, respectively.",

author = "Weihong Wang and Yehee Lee and Lee, \{Tae Gu\} and Bora Mun and Giri, \{Awadut G.\} and Jihye Lee and Hiyoung Kim and Dongyup Hahn and Inho Yang and Jungwook Chin and Hyukjae Choi and Nam, \{Sang Jip\} and Heonjoong Kang",

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doi = "10.1021/ol3019874",

language = "English",

volume = "14",

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T1 - Phorone A and isophorbasone A, sesterterpenoids isolated from the marine sponge Phorbas sp.

AU - Wang, Weihong

AU - Lee, Yehee

AU - Lee, Tae Gu

AU - Mun, Bora

AU - Giri, Awadut G.

AU - Lee, Jihye

AU - Kim, Hiyoung

AU - Hahn, Dongyup

AU - Yang, Inho

AU - Chin, Jungwook

AU - Choi, Hyukjae

AU - Nam, Sang Jip

AU - Kang, Heonjoong

PY - 2012/9/7

Y1 - 2012/9/7

N2 - A chemical investigation of a Korean marine sponge, Phorbas sp., yielded unprecedented sesterterpenoids phorone A (1) and isophorbasone A (2) along with ansellone B (3) and phorbasone A acetate (4). Their complete structures were elucidated by the combination of spectroscopic data and chemical manipulation. Phorone A (1) and isophorbasone A (2) have the new "phorane"(5) and "isophorbasane"(6) sesterterpenoid carbon skeletons, respectively. Ansellone B (3) and phorbasone A acetate (4) exhibited potent inhibitory activity on nitric oxide production in RAW 264.7 LPS-activated mouse macrophage cells with IC50 values of 4.5 and 2.8 μM, respectively.

AB - A chemical investigation of a Korean marine sponge, Phorbas sp., yielded unprecedented sesterterpenoids phorone A (1) and isophorbasone A (2) along with ansellone B (3) and phorbasone A acetate (4). Their complete structures were elucidated by the combination of spectroscopic data and chemical manipulation. Phorone A (1) and isophorbasone A (2) have the new "phorane"(5) and "isophorbasane"(6) sesterterpenoid carbon skeletons, respectively. Ansellone B (3) and phorbasone A acetate (4) exhibited potent inhibitory activity on nitric oxide production in RAW 264.7 LPS-activated mouse macrophage cells with IC50 values of 4.5 and 2.8 μM, respectively.

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DO - 10.1021/ol3019874

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JO - Organic Letters

JF - Organic Letters

IS - 17

ER -

Phorone A and isophorbasone A, sesterterpenoids isolated from the marine sponge Phorbas sp.

Abstract

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